Moral of the story is, don't hire your auntie to bake cookies for labour meetings for half a million a year. Someone might get suspicious.

I always wonder how people who are techincally quite smart and are given so much end up doing such silly things.

What he did might not have been all that silly. It might have been very rational. If he saw that the end was in sight no matter what, whether it was on his terms or those of others, then he might as well get as much out of it as he can. It looks bad on him, but it's a rational choice that was made easier by the weaknesses of the organisation.

It's not unlike the bankers that looked at deregulation and pursued a course that made themselves big enough to recklessly enrich themselves while destroying the economy without seeing any recourse. Only in the case of bankers, it's not about seeing the end of the line, because that simply does not exist for them to the extent that they likely consider it all. But the point is that what appears like silly and ludicrous and reprehensibly irresponsible acts, can be seen as coldly rational calculations that should have been perceived as inevitable given the lack of proper oversight.